For more than two decades, Kyle Sandilands and Jackie ‘O’ Henderson were one of Australian radio’s most familiar partnerships.

They laughed together, argued together and built a career that became almost inseparable from their names.

But now, months after their partnership came to an abrupt end, Sandilands has revealed just how deeply the fallout continues to affect him.

And amid the latest court revelations, he has been left looking back at moments he says he would have handled very differently.

A partnership that once seemed unbreakable

Kyle and Jackie O worked together for more than 25 years, becoming one of the biggest names in Australian commercial radio.

Their partnership eventually ended in dramatic circumstances earlier this year after an on-air argument on February 20.

Henderson subsequently said she could no longer work with Sandilands and did not feel safe in the workplace. The Kyle and Jackie O Show was taken off air in March, while both presenters’ contracts with ARN were terminated.

The breakdown was particularly striking because of how long the pair had worked side by side.

For Sandilands, it was not simply the end of a radio show.

It was the loss of someone who had been an important part of his adult life.

Then came the court documents

The latest emotional chapter began when details contained in Federal Court documents became public.

Henderson has alleged that the nature of their on-air relationship changed from 2023, with behaviour she once viewed as humour or banter becoming increasingly difficult to deal with.

Medical evidence filed in the case includes claims that she developed PTSD linked to her experiences working on the program. These remain allegations being dealt with through the legal process.

Sandilands has strongly disputed the characterisation of their relationship and has said Henderson’s account is not how he remembers their years together.

But reading the allegations has nevertheless forced him to confront the possibility that moments he considered harmless may have affected his former co-host in a very different way.

“If I’d have known…”

One moment in particular has stayed with him.

Sandilands recalled inviting astrophysicist Neil deGrasse Tyson onto the program to challenge astrology — something Henderson was passionate about.

At the time, Sandilands said he believed he was simply “mucking around”.

Looking back now, however, he said he wishes he had understood how deeply it could affect her.

“If I’d have known that was going to cut her to the soul, I would never have done it,” he said.

For him, the painful part is the thought that after three decades of knowing someone, he may not have realised how they were experiencing certain moments.

“That’s her truth. That’s not how I remember it”

Sandilands has stopped short of accepting Henderson’s version of their relationship.

Instead, he acknowledged that two people can experience the same events in completely different ways.

“I’m not angry at Jackie,” he said.

“That’s her truth. That’s not how I remember it.”

The distinction is important as the legal dispute continues, but his comments also reveal the emotional conflict he appears to be carrying — hurt over what has been alleged, while still expressing affection for someone who was once one of the closest people in his professional life.

The memories that won’t leave him

Speaking on Kyle Sandilands Live, he admitted that the affidavit remains on his mind.

“I can’t stop thinking about that affidavit,” he said.

“I can’t stop thinking about Jackie and those things that were written.”

He described trying to occupy himself and move on, only for the thoughts to return.

The emotional toll has also followed him outside the studio.

Sandilands said he has struggled to fully enjoy time with his wife, Tegan Kynaston, and their four-year-old son, Otto, despite trying to focus on his family.

A painful ending to a very long friendship

Perhaps the most revealing part of Sandilands’ comments is that, despite everything that has happened, he says his feelings towards Henderson have not simply disappeared.

“I will love her unconditionally forever even if I never speak to her again,” he said.

“But it is very, very hurtful.”

It is a striking reflection from someone whose public persona has often been built around confidence and provocation.

Behind the microphone, however, the collapse of a 30-year relationship appears to have left him confronting something much harder to joke away.

The radio partnership is over — but the story isn’t

The original Kyle and Jackie O Show ended in March, bringing one of Australia’s most recognisable radio partnerships to a close.

Sandilands later launched his own subscription-based program, Kyle Sandilands Live.

His separate legal dispute with ARN was settled in June for $12.09 million, while Henderson’s legal action remains ongoing. She is seeking more than $82 million and her case is expected to proceed to trial in October.

The latest court developments have therefore reopened a painful chapter rather than closed it.

And for Sandilands, the question is no longer simply why the partnership ended.

It is what might have happened if he had understood earlier just how differently Jackie was experiencing those final years.